Hydrochloric Acid → (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(tert-butylthio)ethyl]piperidine-3-carboxylic acid dihydrochloride

HRID 2186363Notes

Reaction equation

HRID 2186363 reaction equation
[OH-].[Na+].[OH:3][CH:4]([C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][CH:25]=1)[CH2:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][S:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][C@@H:8]1[C:20]([O:22]C)=[O:21].[ClH:36]>CO.O.ClCCl.CO>[ClH:36].[ClH:36].[OH:3][CH:4]([C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][CH:25]=1)[CH2:5][CH2:6][C@@H:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][S:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][C@@H:8]1[C:20]([OH:22])=[O:21]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131723276methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(tert-butylthio)ethyl]piperidine-3-carboxylate

Product 1

HCID 70173521(3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(tert-butylthio)ethyl]piperidine-3-carboxylic acid dihydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
60 °C

Procedure

1 cm3 of 5N aqueous sodium hydroxide solution was added, with stirring and under an inert atmosphere, to a solution of 0.26 g of methyl (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(tert-butylthio)ethyl]piperidine-3-carboxylate in 5 cm3 of methanol. After heating the solution to a temperature in the region of 60° C. and then cooling to room temperature, the reaction mass was evaporated under reduced pressure (2.8 kPa) at a temperature in the region of 60° C. The residue obtained was taken up in 5 cm3 of distilled water and then 5 cm3 of concentrated hydrochloric acid (d=1.18) were added. The mixture was evaporated under reduced pressure (2.8 kPa) at a temperature in the region of 60° C. The residue obtained was taken up in 4 cm3 of a dichloromethane/methanol (90/10 by volume) mixture. The white precipitate obtained was filtered off and washed with 2 times 2 cm3 of this same mixture. The filtrate was concentrated under reduced pressure (2.8 kPa) at a temperature in the region of 40° C. The product obtained was dried under reduced pressure (16 Pa) at a temperature in the region of 60° C. 0.29 g of (3R,4R)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)propyl]-1-[2-(tert-butylthio)ethyl]piperidine-3-carboxylic acid dihydrochloride was obtained in the form of a solid with a beige color melting with softening in the region of 169° C.

Workup

  1. temperaturecooling to room temperature
  2. customthe reaction mass was evaporated under reduced pressure (2.8 kPa) at a temperature in the region of 60° C
  3. customThe residue obtained
  4. customThe mixture was evaporated under reduced pressure (2.8 kPa) at a temperature in the region of 60° C
  5. customThe residue obtained
  6. customThe white precipitate obtained
  7. filtrationwas filtered off
  8. washwashed with 2 times 2 cm3 of this same mixture
  9. concentrationThe filtrate was concentrated under reduced pressure (2.8 kPa) at a temperature in the region of 40° C
  10. customThe product obtained
  11. customwas dried under reduced pressure (16 Pa) at a temperature in the region of 60° C

Sources & evidence

ORD record
ord-d6b40208f92a477e9551b91ad40e0b4e
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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